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CS-W001157 4
Total: USD 88.00

3-Iodonaphthalen-2-amine

  • CAS No. 116632-14-5

  • Cat. No. CS-0134563
  • Molecule weight269.08
  • Purity≥98%
  • MDL No.MFCD12028563

*For research and further manufacturing use only, not for direct human use.

3-Iodonaphthalen-2-amine|CS-0134563

Structure of 116632-14-5

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General Information

  • CAS No. 116632-14-5
  • Cat. No. CS-0134563
  • Purity ≥98%
  • MDL No. MFCD12028563
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈IN
  • Molecular Weight 269.08
  • Synonym(s) 2-Amino-3-iodonaphthalene
  • SMILES NC1=C(I)C=C2C=CC=CC2=C1

Description

3-Iodonaphthalen-2-amine delivers a reactive iodine handle positioned ortho to a primary amine within a rigid naphthalene scaffold. This combination enables efficient coupling in cross-coupling protocols and facilitates conjugation to biomolecules or functional surfaces. The molecule exhibits stability under standard handling conditions and integrates readily into complex molecular architectures requiring site-specific attachment.

Application

3-Iodonaphthalen-2-amine serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to biaryl scaffolds. The iodine substituent facilitates reliable Suzuki, Stille, and Negishi couplings under standard conditions. The naphthalene core provides rigidity and π-conjugation beneficial for materials and pharmaceutical applications. Bench-stable and readily purified by chromatography, it functions effectively in multi-step synthesis workflows requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1
    • Tert-butyl naphthalen-2-ylcarbamate|CS-0465573
      454713-45-2
    • ~45%
    • In-stock
      3-Iodonaphthalen-2-amine|CS-0134563
      116632-14-5

    References

    • SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; CHIOSIS, Gabriela; TALDONE, Tony; SUN, Weilin Patent: WO2011/44394 A1, 2011 ; Location in patent: Page/Page column 119-120 ;
  • Route2
    • null|null
      102153-71-9
    • ~88%
    • In-stock
      3-Iodonaphthalen-2-amine|CS-0134563
      116632-14-5

    References

    • Ma; Liu; Li; Flippen-Anderson; Yu; Cook Journal of Organic Chemistry, 2001 , vol. 66, # 13 p. 4525 - 4542
  • Route3
    • Tert-butyl naphthalen-2-ylcarbamate|CS-0465573
      454713-45-2
    • ~44%
    • In-stock
      3-Iodonaphthalen-2-amine|CS-0134563
      116632-14-5
    • In-stock
      1-Iodonaphthalen-2-amine|CS-0433547
      90016-93-6

    References

    • Taldone, Tony; Zatorska, Danuta; Chiosis, Gabriela Synthetic Communications, 2012 , vol. 42, # 5 p. 635 - 638

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   3.0266
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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